Blog | Entrepreneurship

The Baby Boomer’s Guide to Work After Retirement

Five core strengths to build in order to start your own business after you retire

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At Rich Dad, we’ve talked a lot about how grossly underprepared many people are for retirement. If you go back and read Kim’s and my articles, you’ll fully understand that we have a retirement crisis on our hands.

America’s coming retirement crisis

To make matters worse, the global pandemic caused by the coronavirus is only making things worse.

As PBS writes:

Think of America’s retirement system as a poorly constructed house that has deteriorated with time. Social Security is the financial foundation of retirement, but its trust fund is being rapidly depleted. State and local government pensions were underfunded by $1.2 trillion before the pandemic, according to researchers at the Pew Charitable Trust. About half of private-sector workers lack access to a 401(k) or other employer-sponsored retirement plan.


Roughly 75% of heads of households ages 55 to 65 had almost no chance of being able to fund their retirement needs out of savings before the pandemic, Seitz noted during a recent Milken Institute webinar. But in the past few months, their finances have been deteriorating, with savings ravaged by market volatility, strapped workers tapping their 401(k)s to pay bills and near-retirees losing their jobs.

The article goes on to state that the value of retirement accounts in the US have shrunk by over 4 trillion since the start of the pandemic, with 401Ks shrinking by 19% and IRAs by 14%.

And as Prudential reports:

  • 28 per cent of non-retired adult Americans have no retirement savings or pension (Federal Reserve Board).

  • 52 per cent of households age 55 and older have no retirement savings. Among those with retirement savings, the median amount is approximately $109,000 — enough to generate only about $405 per month of income for a 65-year-old (US Government Accountability Office).

  • Social Security — designed to replace only a portion of workers’ pre-retirement earnings — provides most of the retirement income for about half of households age 65 and older (US Government Accountability Office).

Perhaps you’re feeling the pressure of looming retirement as well. I speak all over the world with people who are urgently looking to grow their financial intelligence through education precisely because they know they need to do something about their retirement now, before it’s too late.

How to have a secure financial future (hint: it’s not saving for retirement)

At Rich Dad, we’re of the firm belief that moving from the left side of the CASHFLOW Quadrant —from employee and self-employed—to the right side of the quadrant—business owner and investor—is the key to securing your financial future, including your retirement.

As I’ve said before, savers are losers. If you think you can save your way to a secure retirement, you’re crazy. If you want true financial freedom after you’re done working, you need to learn how to be an entrepreneur and investor, to operate on the right side of the CASHFLOW Quadrant. In this post, I want to talk about how Baby Boomers can find meaningful work after retirement by being their own boss—by starting their own businesses.

I run into people who are afraid that their window of opportunity may have already closed. Many of these people are in the baby boomer generation who feel it’s too late to start a business.

If you’re in that group, there’s some good news for you. It’s not too late.

Baby boomers are big time entrepreneurs

As CNBC reports, a Kauffman Foundation report shows “Boomers are twice as likely as Millennials to be planning to start a new business. The foundation also found in their 2016 Startup Index that 24.3% of all new entrepreneurs fall between the ages of 55 and 64.”

Moreover, the report shows that while millennials make up 25% of all entrepreneurs, that number is in the decline and “the Boomer percentage has been quickly increasing.”

The Kauffman Foundation report defines one quality that helps baby boomers become successful entrepreneurs: experience.

While the young may have high energy and passion, they can’t beat the boomer’s experience both on a personal and a professional level.

Work after retirement and why baby boomer entrepreneurship is on the rise

Now, why would baby boomers start new companies rather than retire? The short question is that they’re not in a position to retire in the traditional sense. As my wife, Kim, wrote a while ago:

  • 74% of workers expect to continue working in retirement to contribute, at least a small part, to their retirement income

  • 36% of workers are actually dreading retirement
  • That’s not surprising, given that “One in three Americans has absolutely nothing saved for retirement.” With so many people unprepared for their retirement, it’s no wonder that they continue to work hard well into their golden years.

For certain folks, the prospect of working after retirement can seem like a big negative. But as Kim points out, a change of mindset can open up new possibilities:

Retirement doesn’t have to be an extension of the Rat Race. In fact, retirement can and should be some of the best years of your lives. Consider taking an alternate approach to your retirement. One that defies working harder, for longer, just to get by…Work in our retirement stopped being about the daily stresses of paying bills and having enough income to live on. Instead, we got to focus on the work we were passionate about – building our business educating others on financial literacy. We didn’t work because we had to – we worked because we wanted to, and that made a huge difference.

So, there are two bits of good news, actually: you aren’t too old to start a business (even if you’re coming up or at retirement age), and it can be a lot of fun.

Five entrepreneurship strengths for baby boomers to build

If you’re attracted to the idea of being an entrepreneur in your retirement years, you need to know it’s a muscle you need to build. Here are five strengths that are required to be a successful entrepreneur:

  • Have a thick skin

    It seems that as soon as you announce you are starting a business everyone is an expert in starting a business. Not everyone will love your idea or product, and they won’t be afraid to tell you. I’m not saying you shouldn’t listen to criticism, but you have to be able to take the punches and not take everything personally.

  • Get used to being constantly connected

    As an entrepreneur, there really isn’t such a thing as “disconnecting” from the world, not in the beginning anyway. You’ll be living and breathing your new company while trying to educate everyone about your business. You’ll be constantly thinking about how to improve things, reduce costs, and sell more. There is no such thing as a 9-to-5 work schedule when you’re an entrepreneur.

  • Don’t look for constant praise

    If you’re an employee, you’re probably used to getting constant feedback about your performance, tasks, and project completion. A lot of employees are even used to their bosses telling them how great they are—even if they know they aren’t. This is not the case for an entrepreneur. You won’t hear any of that unless you tell yourself. Your praise comes in the form of making money. And it’s going to be a while before you really get the praise you’re looking for.

  • Become your own motivation

    Similar to needing praise, if you need external motivation, you shouldn’t be an entrepreneur either. When you wake up in the morning as an entrepreneur, there isn’t someone standing in your kitchen ready to give you that day’s tasks. It’s all on you. Get comfortable with being the person who motivates you to keep going each morning.

  • Learn to wear multiple hats

    There are people I know that are only comfortable being an accountant, or a writer, or an event planner. These people are only comfortable doing one thing and, as such, should never be an entrepreneur. As an entrepreneur, especially a solopreneur, you are often putting on different hats, making a multitude of decisions and you need to be confident in doing so.

Baby boomer business plan

There’s a lot more that goes into starting a company, from business plans to corporate structures to getting the right funding. But these core strengths are the foundation by which all those other things become successful. Because it all starts with mindset. If you don’t have the right one, all your efforts will be doomed to fail.

So, today, take a look in the mirror and ask, “How am I doing in these five areas?” If you find you need work in one area or more, build a plan and get to work today.

Original publish date: September 05, 2017

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